Diphenhydramine
Identification
- Name
- Diphenhydramine
- Accession Number
- DB01075 (APRD00587, DB06975)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
Diphenhydramine - perhaps known most commonly as its brand name formulation Benadryl - is a first-generation H1 receptor antihistamine that is used extensively for the treatment of seasonal allergies, insect bites and stings, and rashes [9, 10, 11, 15]. However, it also has antiemetic, antitussive, hypnotic, and antiparkinson properties [11, 14]. As histamine receptors exist both peripherally and in the central nervous system, diphenhydramine has been shown to cause sedation due to its competitive antagonism of histamine H1 receptors within the central nervous system [9, 10, 11, 15, 5]. While its use in allergy therapy can sometimes fall out of favor due to its sedative effect, diphenhydramine has been repurposed for use within many non-prescription over-the-counter sleep aids and cough-and-cold medications that have been marketed for "night time" use [9, 12, 13].
Diphenhydramine is also used in combination with 8-chlorotheophylline as the anti-nausea drug Dimenhydrinate where it is utilized primarily for its antagonism of H1 histamine receptors within the vestibular system [4].
Diphenhydramine has also been shown to be implicated in a number of neurotransmitter systems that affect behaviour including dopamine, norepinephrine, serotonin, acetylcholine, and opioid [3]. As a result, diphenhydramine is being investigated for its anxiolytic and anti-depressant properties.
- Structure
Structure for Diphenhydramine (DB01075)
- Synonyms
- 2-(Benzhydryloxy)-N,N-dimethylethylamine
- 2-diphenylmethoxy-N,N-demthylethanamine
- alpha-(2-Dimethylaminoethoxy)diphenylmethane
- beta-Dimethylaminoethanol diphenylmethyl ether
- beta-Dimethylaminoethyl benzhydryl ether
- Difenhidramina
- Diphenhydramine
- Diphenhydraminum
- N-(2-(Diphenylmethoxy)ethyl)-N,N-dimethylamine
- O-benzhydryldimethylaminoethanol
- β-dimethylaminoethyl benzhydryl ether
- Product Ingredients
Ingredient UNII CAS InChI Key Diphenhydramine citrate 4OD433S209 88637-37-0 SPCKHVPPRJWQRZ-UHFFFAOYSA-N Diphenhydramine hydrochloride TC2D6JAD40 147-24-0 PCHPORCSPXIHLZ-UHFFFAOYSA-N Diphenhydramine methylbromide UJO67AO8YI 31065-89-1 BDQPXVWYFLTETB-UHFFFAOYSA-M Diphenhydramine salicylate 707L3YC54L 7491-10-3 RTSZUSOHOIFYSY-UHFFFAOYSA-N - Active Moieties
Name Kind UNII CAS InChI Key Phenol unknown 339NCG44TV 108-95-2 ISWSIDIOOBJBQZ-UHFFFAOYSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Benadryl Injection, solution 50 mg/1mL Intramuscular; Intravenous Parke Davis Div Of Pfizer Inc 1947-03-06 2008-01-31 US 
Benadryl Injection, solution 50 mg/1mL Intramuscular; Intravenous Parke Davis Div Of Pfizer Inc 1957-12-30 2007-01-31 US Benadryl Inj. 50mg/ml Liquid 50 mg Intramuscular; Intravenous Warner Lambert Canada Inc. 1994-12-31 2000-11-27 Canada 
Diphenhydramine HCl Inj USP 50mg/ml Liquid 50 mg Intravenous International Medication Systems, Limited 1974-12-31 1997-08-15 Canada Diphenhydramine HCl Injection, USP Solution 50 mg Intramuscular; Intravenous Sterimax Inc 1994-12-31 Not applicable Canada Diphenhydramine Hydrochloride Injection Solution 50 mg Intramuscular; Intravenous Fresenius Kabi 2012-02-17 Not applicable Canada Diphenhydramine Hydrochloride Injection USP Liquid 50 mg Intramuscular; Intravenous Sandoz Canada Incorporated 1983-12-31 Not applicable Canada Diphenist 50mg/ml Liquid 50 mg Intramuscular; Intravenous Omega Laboratories Ltd 1997-10-28 Not applicable Canada Scheinpharm Diphenhydramine Inj.50mg/ml Solution 50 mg Intramuscular; Intravenous Schein Pharmaceutical Canada Inc. 1996-09-30 2004-07-26 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Diphendydramine Hydrochloride Capsule 25 mg/1 Oral Remedy Repack 2010-12-17 2017-04-24 US 
Diphenhydramine Injection, solution 50 mg/1mL Intramuscular; Intravenous Fresenius Kabi USA, LLC 2002-08-01 Not applicable US Diphenhydramine Injection, solution 50 mg/1mL Intravenous Remedy Repack 2013-11-18 2017-01-20 US Diphenhydramine Injection, solution 50 mg/1mL Intramuscular; Intravenous Micro Labs Limited 2018-12-04 Not applicable US Diphenhydramine Hci Injection, solution 50 mg/1mL Intramuscular; Intravenous HF Acquisition Co LLC, DBA HealthFirst 2018-11-19 Not applicable US Diphenhydramine Hydrochloride Injection 50 mg/1mL Intramuscular; Intravenous TYA Pharmaceuticals 1972-11-27 Not applicable US Diphenhydramine Hydrochloride Injection 50 mg/1mL Intramuscular; Intravenous Nucare Pharmaceuticals,inc. 1972-11-27 Not applicable US Diphenhydramine Hydrochloride Injection, solution 50 mg/1mL Intramuscular; Intravenous General Injectables and Vaccines 2010-03-01 Not applicable US Diphenhydramine Hydrochloride Injection 50 mg/1mL Intramuscular; Intravenous Hf Acquisition Co. Llc, Dba Health First 2018-08-16 Not applicable US Diphenhydramine Hydrochloride Capsule 50 mg/1 Oral Cardinal Health 2011-01-20 2018-06-04 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 7 Select Allergy Tablet 25 mg/1 Oral 7 Eleven 2014-04-22 Not applicable US 7 Select Allergy Childrens Solution 12.5 mg/5mL Oral 7 Eleven 2014-08-05 Not applicable US 7 Select Night Time Sleep Aid Solution 50 mg/30mL Oral 7 Eleven 2014-04-22 Not applicable US Adult Allergy Solution 50 mg/20mL Oral Chain Drug Consortium 2015-05-04 Not applicable US Adult Allergy Relief Solution 50 mg/20mL Oral Walmart Stores 2017-05-03 Not applicable US After Bite Outdoor Gel 20 mg/1mL Topical Tender Corporation 2016-11-01 2018-03-01 US After Bite Outdoor Gel 20 mg/1g Topical Tender Corporation 2018-03-01 Not applicable US After Bite Plus Cream 20 mg/1mL Topical Tender Corporation 2012-07-03 2018-03-06 US After Bite Plus Gel 20 mg/1g Topical Tender Corporation 2018-03-01 Not applicable US After Bite Xtra Gel 20 mg/1g Topical Tender Corporation 2018-03-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End 7 Select Ibuprofen PM Diphenhydramine citrate (38 mg/1) + Ibuprofen (200 mg/1) Tablet, film coated Oral 7 Eleven 2014-08-05 Not applicable US 7 Select Night Time Severe Cold Cough and Flu Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) + Phenylephrine hydrochloride (10 mg/1) Powder, for solution Oral 7-Eleven 2016-01-25 Not applicable US 7 Select Night Time severe cold, cough and flu Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) + Phenylephrine hydrochloride (10 mg/1) Powder, for solution Oral 7 Eleven 2015-11-12 2017-08-01 US 7 Select Pain Relief PM Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1) Tablet, film coated Oral 7 Eleven 2014-09-04 2016-07-22 US 7-Select Advil PM Diphenhydramine citrate (38 mg/1) + Ibuprofen (200 mg/1) Tablet, coated Oral Lil' Drug Store Products, Inc. 2011-06-01 2017-12-31 US Acedif PLUS Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1) Tablet Oral Plus Distributors LLC 2019-02-01 Not applicable US Aceta-gesic Diphenhydramine hydrochloride (12.5 mg/1) + Acetaminophen (325 mg/1) Tablet, coated Oral Rugby 2014-06-30 Not applicable US Aceta-gesic Diphenhydramine hydrochloride (12.5 mg/1) + Acetaminophen (325 mg/1) Tablet, coated Oral Remedy Repack 2014-08-08 Not applicable US Acetadryl Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1) Tablet, film coated Oral Aidarex Pharmaceuticals LLC 2011-07-21 Not applicable US Acetadryl Diphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1) Tablet, film coated Oral Physicians Science & Nature Inc. 2011-07-21 2016-05-31 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Airacof Diphenhydramine hydrochloride (12.5 mg/5mL) + Codeine phosphate hemihydrate (7.5 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL) Liquid Oral Centurion Labs 2010-01-08 2016-05-02 US Benadryl Diphenhydramine hydrochloride (50 mg/1mL) Injection, solution Intramuscular; Intravenous Physicians Total Care, Inc. 1994-06-01 2010-12-29 US Benadryl Diphenhydramine hydrochloride (50 mg/1mL) Injection, solution Intramuscular; Intravenous Physicians Total Care, Inc. 2006-01-13 2010-12-29 US Contrast Allergy PreMed Pack Diphenhydramine hydrochloride (50 mg/50mg) + Prednisone (50 mg/50mg) Kit Shertech Laboratories, Llc 2016-09-13 Not applicable US Dicopanol Diphenhydramine hydrochloride (0.86 g/0.86g) Kit Oral California Pharmaceuticals, Llc 2016-01-01 Not applicable US Dicopanol Diphenhydramine hydrochloride (0.75 g/0.75g) Kit Oral Fusion Pharmaceuticals LLC 2010-02-08 Not applicable US DiphenMax Diphenhydramine (25 mg/1) + Phenylephrine (10 mg/1) Tablet, chewable Oral River's Edge Pharmaceuticals, LLC 2008-01-01 2009-11-09 US Endal CD Diphenhydramine hydrochloride (10 mg/5mL) + Codeine phosphate hemihydrate (7.5 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL) Syrup Oral Tiber Laboratories 2009-12-09 2009-12-31 US FIRST BXN Mouthwash Diphenhydramine hydrochloride (0.84 mg/1mL) + Lidocaine hydrochloride (6.75 mg/1mL) + Nystatin (6.75 mg/1mL) Kit Oral CutisPharma, Inc 2009-09-08 Not applicable US FIRST Dukes Mouthwash Compounding Diphenhydramine hydrochloride (0.525 g/0.525g) + Hydrocortisone (0.06 g/0.06g) + Nystatin (0.6 g/0.6g) Kit Oral CutisPharma, Inc. 2010-12-15 Not applicable US - International/Other Brands
- Aleryl / Alledryl / Allerdryl (Valeant) / Baramine / Beldin / Belix / Benylan (Biogen) / Dermodrin (Montavit) / Desentol (Meda) / Dibondrin (Montavit) / Dimedrol (Zdorovie) / Diphen (Wockhardt) / Dormarex 2 / Genahist / Histaxin (Meda) / Hyrexin (Hyrex) / Nytol Quickgels (GlaxoSmithKline) / Restamin (Kowa Souyaku) / Siladryl / Silphen Cough
- Categories
- Agents producing tachycardia
- Amines
- Aminoalkyl Ethers
- Anesthetics
- Anesthetics, Local
- Anti-Allergic Agents
- Anticholinergic Agents
- Antiemetics
- Antihistamines for Systemic Use
- Antihistamines for Topical Use
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Benzene Derivatives
- Benzhydryl Compounds
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Ethanolamine Derivatives
- Ethylamines
- First Generation Antihistamines
- Gastrointestinal Agents
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Hypnotics and Sedatives
- Muscarinic Antagonists
- OCT2 Inhibitors
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Sleep Aids, Pharmaceutical
- UNII
- 8GTS82S83M
- CAS number
- 58-73-1
- Weight
- Average: 255.3547
Monoisotopic: 255.162314299 - Chemical Formula
- C17H21NO
- InChI Key
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
- IUPAC Name
- [2-(diphenylmethoxy)ethyl]dimethylamine
- SMILES
- CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
Pharmacology
- Indication
Diphenhydramine is a first-generation histamine H1 receptor antagonist (H1 antihistamine) that is widely available as a non-prescription, over-the-counter (OTC) medication. As an OTC medication, diphenhydramine is typically formulated as tablets and creams indicated for use in treating sneezing, runny nose, itchy/watery eyes, itching of nose or throat, insomnia, pruritis, urticaria, insect bites/stings, allergic rashes, and nausea [9, 10, 11, 15, 5].
Additionally, when the use of oral diphenhydramine is impractical, there are also prescription-only formulations such as diphenhydramine injection products that are effective in adults and pediatric patients (other than premature infants and neonates) for: i) the amelioration of allergic reactions to blood or plasma, in anaphylaxis as an adjunct to epinephrine and other standard measures after acute allergic reaction symptoms have been controlled, and for other uncomplicated allergic conditions of the immediate type when oral therapy is impossible or contraindicated [14]; ii) the active treatment of motion sickness [14]; and iii) use in parkinsonism when oral therapy is impossible or contraindicated, as follows: parkinsonism in the elderly who are unable to tolerate more potent agents; mild cases of parkinsonism in other age groups, and in other cases of parkinsonism in combination with centrally acting anticholinergic agents [14].
- Associated Conditions
- Pharmacodynamics
Diphenhydramine has anti-histaminic (H1-receptor), anti-emetic, anti-vertigo and sedative and hypnotic properties [12]. The anti-histamine action occurs by blocking the spasmogenic and congestive effects of histamine by competing with histamine for H1 receptor sites on effector cells, preventing but not reversing responses mediated by histamine alone [12]. Such receptor sites may be found in the gut, uterus, large blood vessels, bronchial muscles, and elsewhere [12]. Anti-emetic action is by inhibition at the medullary chemoreceptor trigger zone [12]. Anti-vertigo action is by a central antimuscarinic effect on the vestibular apparatus and the integrative vomiting center and medullary chemoreceptor trigger zone of the midbrain [12].
- Mechanism of action
Diphenhydramine predominantly works via the antagonism of H1 (Histamine 1) receptors [9, 10, 11, 15, 5]. Such H1 receptors are located on respiratory smooth muscles, vascular endothelial cells, the gastrointestinal tract (GIT), cardiac tissue, immune cells, the uterus, and the central nervous system (CNS) neurons [9, 10, 11, 15, 5]. When the H1 receptor is stimulated in these tissues it produces a variety of actions including increased vascular permeability, promotion of vasodilation causing flushing, decreased atrioventricular (AV) node conduction time, stimulation of sensory nerves of airways producing coughing, smooth muscle contraction of bronchi and the GIT, and eosinophilic chemotaxis that promotes the allergic immune response [9, 10, 11, 15, 5].
Ultimately, diphenhydramine functions as an inverse agonist at H1 receptors, and subsequently reverses effects of histamine on capillaries, reducing allergic reaction symptoms [9, 10, 11, 15, 5]. Moreover, since diphenhydramine is a first-generation antihistamine, it readily crosses the blood-brain barrier and inversely agonizes the H1 CNS receptors, resulting in drowsiness, and suppressing the medullary cough center [9, 10, 11, 15, 5].
Furthermore, H1 receptors are similar to muscarinic receptors [9, 10, 11, 15, 5]. Consequently, diphenhydramine also acts as an antimuscarinic [9, 10, 11, 15, 5]. It does so by behaving as a competitive antagonist of muscarinic acetylcholine receptors, resulting in its use as an antiparkinson medication [9, 10, 11, 15, 5].
Lastly, diphenhydramine has also demonstrated activity as an intracellular sodium channel blocker, resulting in possible local anesthetic properties [9].
Target Actions Organism AHistamine H1 receptor antagonistHumans UMuscarinic acetylcholine receptor M2 antagonistHumans - Absorption
Diphenhydramine is quickly absorbed after oral administration with maximum activity occurring in approximately one hour [6, 13]. The oral bioavailability of diphenhydramine has been documented in the range of 40% to 60%, and peak plasma concentration occurs about 2 to 3 hours after administration [6, 13].
- Volume of distribution
Diphenhydramine is widely distributed throughout the body, including the CNS [16]. Following a 50 mg oral dose of diphenhydramine, the volume of distribution is in the range of 3.3 - 6.8 l/kg [16].
- Protein binding
Some prescribing information records the protein binding of diphenhydramine as approximately 78% [16] while others have suggested the medication is about 80 to 85% [13] bound to plasma proteins.
- Metabolism
Diphenhydramine undergoes rapid and extensive first-pass metabolism [16, 13, 8]. In particular, two successive N-demethylations occur wherein diphenhydramine is demethylated to N-desmethyldiphenhydramine (the N-desmethyl metabolite) and then this metabolite is itself demethylated to N,N-didesmethyldiphenhydramine (the N,N-didesmethyl metabolite) [16, 8]. Subsequently, acetyl metabolites like N-acetyl-N-desmethyldiphenhydramine are generated via the amine moiety of the N,N-didesmethyl metabolite [8]. Additionally, the N,N-didesmethyl metabolite also undergoes some oxidation to generate the diphenylmethoxyacetic acid metabolite as well [16, 13, 8]. The remaining percentage of a dose of administered diphenhydramine is excreted unchanged [16, 13, 8]. The metabolites are further conjugated with glycine and glutamine and excreted in urine [13].
Moreover, studies have determined that a variety of cytochrome P450 isoenzymes are involved in the N-demethylation that characterizes the primary metabolic pathway of diphenhydramine, including CYP2D6, CYP1A2, CYP2C9, and CYP2C19 [7]. In particular, CYP2D6 demonstrates higher affinity catalysis with the diphenhydramine substrate than the other isoenzymes identified [7]. Consequently, inducers or inhibitors of these such CYP enzymes may potentially affect the serum concentration and incidence and/or severity of adverse effects associated with exposure to diphenhydramine [7].
- Route of elimination
The metabolites of diphenhydramine are conjugated with glycine and glutamine and excreted in urine [12, 13]. Only about 1% of a single dose is excreted unchanged in urine [12, 13]. The medication is ultimately eliminated by the kidneys slowly, mainly as inactive metabolites [12, 13].
- Half life
The elimination half-life ranges from 2.4-9.3 hours in healthy adults [16, 13]. The terminal elimination half-life is prolonged in liver cirrhosis [13].
- Clearance
Values for plasma clearance of a 50 mg oral dose of diphenhydramine has been documented as lying in the range of 600-1300 ml/min [16].
- Toxicity
Overdose is expected to result in effects similar to the adverse effects that are ordinarily associated with the use of diphenhydramine, including drowsiness, hyperpyrexia, and anticholinergic effects, among others [10, 11, 12, 13, 16]. Additional symptoms during overdose may include mydriasis, fever, flushing, agitation, tremor, dystonic reactions, hallucinations and ECG changes [13]. Large overdose may cause rhabdomyolysis, convulsions, delirium, toxic psychosis, arrhythmias, coma and cardiovascular collapse [13]. Moreover, with higher doses, and particularly in children, symptoms of CNS excitation including hallucinations and convulsions may appear; with massive doses, coma or cardiovascular collapse may follow [16].
Although diphenhydramine has been in widespread use for many years without ill consequence, it is known to cross the placenta and has been detected in breast milk [16]. This medication should therefore only be used when the potential benefit of treatment to the mother exceeds any possible hazards to the developing fetus or suckling infant [16].
Pharmacokinetic studies indicate no major differences in the distribution or elimination of diphenhydramine compared to younger adults [16]. Nevertheless, diphenhydramine should be used with caution in the elderly, who are more likely to experience adverse effects [13]. Avoid use in elderly patients with confusion [13].
The results of a review on the use of diphenhydramine in renal failure suggest that in moderate to severe renal failure, the dose interval should be extended by a period dependent on Glomerular filtration rate (GFR) [16].
After intravenous administration of 0.8 mg/kg diphenhydramine, a prolonged half-life was noted in patients with chronic liver disease which correlated with the severity of the disease [16]. However, the mean plasma clearance and apparent volume of distribution were not significantly affected [16].
LD50=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Diphenhydramine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (S)-Warfarin The metabolism of (S)-Warfarin can be decreased when combined with Diphenhydramine. 1,10-Phenanthroline The therapeutic efficacy of Diphenhydramine can be decreased when used in combination with 1,10-Phenanthroline. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3,4-Methylenedioxyamphetamine The risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 3,4-Methylenedioxyamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when Diphenhydramine is combined with 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 5-methoxy-N,N-dimethyltryptamine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Diphenhydramine is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. - Food Interactions
- Avoid alcohol.
- Take with food.
References
- Synthesis Reference
Alison B. Lukacsko, Joseph J. Piala, "Effect of a combination of a terbutaline, diphenhydramine and ranitidine composition on gastrointestinal injury produced by nonsteroidal anti-inflammatory compositions." U.S. Patent US5260333, issued December, 1983.
US5260333- General References
- Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. [PubMed:16680933]
- Abdi A, Rose E, Levine M: Diphenhydramine overdose with intraventricular conduction delay treated with hypertonic sodium bicarbonate and i.v. lipid emulsion. West J Emerg Med. 2014 Nov;15(7):855-8. doi: 10.5811/westjem.2014.8.23407. Epub 2014 Sep 19. [PubMed:25493135]
- Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [PubMed:11835984]
- Jaju BP, Wang SC: Effects of diphenhydramine and dimenhydrinate on vestibular neuronal activity of cat: a search for the locus of their antimotion sickness action. J Pharmacol Exp Ther. 1971 Mar;176(3):718-24. [PubMed:4329456]
- Flake ZA, Scalley RD, Bailey AG: Practical selection of antiemetics. Am Fam Physician. 2004 Mar 1;69(5):1169-74. [PubMed:15023018]
- Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055]
- Akutsu T, Kobayashi K, Sakurada K, Ikegaya H, Furihata T, Chiba K: Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088. Epub 2006 Oct 4. [PubMed:17020955]
- Rodrigues WC, Castro C, Catbagan P, Moore C, Wang G: Immunoassay screening of diphenhydramine (Benadryl(R)) in urine and blood using a newly developed assay. J Anal Toxicol. 2012 Mar;36(2):123-9. doi: 10.1093/jat/bkr015. [PubMed:22337782]
- StatPearls [Internet]: Diphenhydramine [Link]
- Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Tablets Patient Information [Link]
- Electronic Medicines Compendium: Histergan (diphenhydramine hydrochloride) Cream Monograph [Link]
- Electronic Medicines Compendium: Boots Sleepeaze (diphenhydramine hydrochloride) 50mg Tablets Monograph [Link]
- Electronic Medicines Compendium: Nytol One-A-Night (diphenhydramine hydrochloride) Monograph [Link]
- Diphenhydramine Hydrochloride Injection, USP FDA Label [File]
- DIPHENHYDRAMINE- diphenhydramine hcl tablet, coated DailyMed FDA Label [File]
- Benylin Chesty Coughs UK MHRA Product Information [File]
- External Links
- Human Metabolome Database
- HMDB0001927
- KEGG Drug
- D00300
- KEGG Compound
- C06960
- PubChem Compound
- 3100
- PubChem Substance
- 46505484
- ChemSpider
- 2989
- BindingDB
- 50017674
- ChEBI
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- ChEMBL
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- GtP Drug Page
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- RxList
- RxList Drug Page
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- Wikipedia
- Diphenhydramine
- ATC Codes
- D04AA32 — Diphenhydramine
- D04AA — Antihistamines for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- R06AA — Aminoalkyl ethers
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- D04AA — Antihistamines for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- AHFS Codes
- 04:04.04 — Ethanolamine Derivatives
- 04:04.00 — First Generation Antihistamines
- PDB Entries
- 2aot
- MSDS
- Download (73.5 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advance Pharmaceutical
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- Amend
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- Diversified Healthcare Services Inc.
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- Sandhills Packaging Inc.
- Scientific Laboratories Inc.
- Silarx Pharmaceuticals
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Tya Pharmaceuticals
- UDL Laboratories
- United Research Laboratories Inc.
- Vangard Labs Inc.
- Walgreen Co.
- Dosage forms
Form Route Strength Kit Topical Capsule; kit Oral Capsule Oral Cream Topical 20 mg/1mL Cream Topical 2.0 mL/100mL Liquid Oral 12.5 mg/5mL Capsule, gelatin coated Oral Powder Oral 25 mg/1 Cream Topical Liquid Oral 12.5 mg Solution Oral 12.5 mg Gel Topical 2 g/100g Cream Topical 2.0 % Patch Topical Syrup Oral Injection, solution Intramuscular; Intravenous 50 mg/1mL Tablet Oral 25 mg Tablet, coated Oral 25 mg/1 Strip Oral 25 mg/1 Tablet, chewable Oral 12.5 mg Liquid Topical Liquid Oral 6.25 mg Cream Topical 2 % Elixir Oral 12.5 mg Gel Topical 20 mg/1mL Tablet, chewable Oral 25 mg Gel Topical 2 % Spray Topical Tablet Oral 25 mg/250mg Strip Oral 25 mg Lotion Topical Suspension Topical Liquid Oral Tablet, coated Oral 25 mg/ 11 Syrup Oral 6.25 mg Tablet Oral 19 mg Strip Oral 19 mg Suspension Oral Tablet Oral 12.5 mg/1 Tablet, chewable Oral 12.5 mg/1 Kit; tablet Oral Ointment Topical Kit Oral 0.75 g/0.75g Kit Oral 0.86 g/0.86g Tablet Oral 38.0 mg Capsule, coated Oral 25 mg/1 Injection, solution Intravenous 50 mg/1mL Capsule, liquid filled Oral 20 mg/1 Tablet Oral 50 mg/1 Liquid Intravenous 50 mg Capsule Oral 25 mg/1 Capsule Oral 50 mg/1 Capsule, liquid filled Oral 50 mg/1 Elixir Oral 25 mg/10mL Injection Intramuscular 50 mg/1mL Injection Intramuscular; Intravenous 50 mg/1mL Injection Parenteral 50 mg/1mL Solution Oral 25 mg/10mL Solution Oral 50 mg/20mL Tablet, film coated Oral 25 mg/1 Liquid Intramuscular; Intravenous 50 mg Tablet, chewable Oral Kit Oral; Topical Gel Topical 2 mg/100mL Capsule, liquid filled Oral Capsule, liquid filled Oral 25 mg/1 Solution Oral 50 mg/40mL Kit Oral Aerosol, spray Topical Solution Oral 50 mg/30mL Liquid Topical 20.3 g/1L Spray Topical 2 g/100mL Gel Topical 2.03 g/100g Aerosol Topical Solution Topical Strip Oral 12.5 mg Tablet Oral 12.5 mg Tablet, orally disintegrating Oral 12.5 mg/1 Liniment Topical Liquid Oral 50 mg/20mL Capsule, gelatin coated Oral 50 mg/1 Kit Lozenge Oral 25 mg Strip Oral Capsule Oral 25 mg Liquid Oral 50 mg/30mL Solution Oral 50 mg Tablet, film coated Oral 50 mg/1 Capsule, liquid filled Oral 50 mg/21 Powder Oral Solution Oral Tablet Oral 50 mg Granule, for solution Oral Tablet, coated Oral Elixir Oral 2.5 mg Solution Oral 12.5 mg/5mL Syrup Oral 12.5 mg/5mL Gel Topical 20.5 mg/1mL Solution Intramuscular; Intravenous 50 mg Gel Topical 2 g/100mL Gel Topical .2 g/10mL Tablet Oral Tablet, coated Oral 50 mg/1 Gel Topical Tablet, multilayer Oral Tablet, multilayer, extended release Oral Gel Topical 20 mg/1g Spray Topical 20 mg/1mL Capsule, coated Oral Tablet Oral 25 mg/1 Tablet, film coated Oral Tablet, delayed release Oral Capsule Oral 50 mg Tablet, chewable Oral 25 mg/1 Powder, for solution Oral Liquid Oral 6.25 mg/1mL Liquid Oral 25 mg/10mL Capsule, gelatin coated Oral 50 mg/21 Spray Topical 2.0 % Liquid Oral 50 mg Capsule, gelatin coated Oral 25 mg/1 - Prices
Unit description Cost Unit DiphenhydrAMINE HCl 100 50 mg capsule Bottle 13.99USD bottle Diphenhydramine 50 mg/ml 3.94USD ml Diphenhydramine 50 mg/ml vial 1.69USD ml DiphenhydrAMINE HCl 50 mg/ml vial 1.44USD vial Dytan 25 mg tablet chewable 1.37USD tablet Benadryl 50 mg/ml vial 1.36USD ml Diphenmax 25 mg tablet 1.24USD tablet Benadryl allergy 25 mg strips 0.45USD strip Unisom sleep aid tablet 0.34USD tablet Sleep-eze 3 tablet 0.29USD tablet Compoz 50 mg tablet 0.27USD tablet Sominex max str 50 mg caplet 0.27USD caplet Benadryl allergy fastmelt tablet 0.26USD tablet Unisom 25 mg sleeptabs 0.25USD tablet Unisom 50 mg sleepgels 0.25USD each Unisom sleepmelts 25 mg tablet 0.24USD tablet Nytol 25 mg tablet 0.23USD tablet Benadryl allergy-sinus caplet 0.22USD caplet Compoz 25 mg gelcap 0.2USD capsule Benadryl allergy 25 mg softgel 0.19USD softgel capsule Benadryl allergy 25 mg ultratab 0.19USD tablet Benadryl allergy-cold kapgels 0.19USD each Benadryl allergy-sinus kapgels 0.19USD each Benadryl-d allergy-sinus ultratab 0.19USD tablet Diphenhydramine hcl powder 0.17USD g Eql allergy 25 mg tablet 0.17USD tablet Nighttime sleep aid 25 mg cplt 0.17USD caplet Banophen anti-itch 2% cream 0.16USD g Benadryl itch relief stick 0.16USD ml Sominex 25 mg tablet 0.16USD tablet Benadryl allergy 25 mg kapgels 0.15USD each Allergy 25 mg tablet 0.14USD tablet Benadryl 25 mg kapseals 0.14USD each Benadryl itch stopping crm 0.14USD g DiphenhydrAMINE HCl 25 mg capsule 0.13USD capsule Diphenhist with zinc cream 0.12USD g Ra allergy 25 mg tablet 0.12USD tablet CVS Pharmacy allergy 25 mg tablet 0.11USD tablet Diphenhydramine 25 mg minitab 0.11USD tablet Simply sleep 25 mg caplet 0.11USD caplet Sleep ii tablet 0.11USD tablet Diphenhydramine 50 mg capsule 0.1USD capsule Benadryl 2% spray 0.09USD ml Diphenhist 50 mg tablet 0.09USD tablet Genahist 25 mg tablet 0.09USD tablet Ra sleep tablet 0.09USD tablet Banophen 25 mg tablet 0.08USD tablet Wal-dryl anti-itch spray 0.08USD ml CVS Pharmacy allergy 25 mg caplet 0.07USD caplet Nighttime sleep aid 25 mg caplet 0.07USD caplet CVS Pharmacy itch relief spray 0.06USD ml Diphen 25 mg capsule 0.06USD capsule Diphenhist 25 mg caplet 0.06USD caplet Benadryl anti-itch 0.45% gel 0.05USD g Diphenhydramine 50 mg caplet 0.05USD caplet Benadryl itch stopping gel 0.04USD g Child benadryl-d aller-sin liquid 0.04USD ml Diphenhydramine 25 mg capsule 0.04USD capsule Vicks 44d cough & head liquid 0.03USD ml Vicks 44e cough & chest liquid 0.03USD ml Banophen allergy liquid 0.02USD ml Diphenhydramine 25 mg tablet 0.02USD tablet Ra anti-tussive dm syrup 0.02USD ml Siladryl 12.5 mg/5 ml liquid 0.02USD ml Silphen cough syrup 0.02USD ml Silphen dm cough syrup 0.02USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US8883849 No 2014-11-11 2022-01-17 US US9155718 No 2015-10-13 2022-01-17 US US8263647 No 2012-09-11 2022-05-30 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 161-162 Martin, H., Hafliger, F.,Gatzi, K.and Grob, A.; U.S. Patent 2,397,799; April 2,1946; assigned to J.R. Geigy AG, Switzerland. Rieveschl, G. Jr.; U.S. Patent 2,421,714; June 3,1947; assigned to Parke, Davis & Co. Rieveschl, G. Jr.; U.S. Patent 2,427,878; September 23,1947; assigned to Parke, Davis & Company. boiling point (°C) 150-165 °C at 2.00E+00 mm Hg PhysProp water solubility 3060 mg/L (at 37 °C) BEILSTEIN logP 3.27 HANSCH,C ET AL. (1995) pKa 8.98 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0752 mg/mL ALOGPS logP 3.44 ALOGPS logP 3.65 ChemAxon logS -3.5 ALOGPS pKa (Strongest Basic) 8.87 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 12.47 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 79.93 m3·mol-1 ChemAxon Polarizability 29.86 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9898 Blood Brain Barrier + 0.9381 Caco-2 permeable + 0.8744 P-glycoprotein substrate Substrate 0.6211 P-glycoprotein inhibitor I Non-inhibitor 0.6632 P-glycoprotein inhibitor II Non-inhibitor 0.8381 Renal organic cation transporter Inhibitor 0.7752 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.6173 CYP450 1A2 substrate Inhibitor 0.8306 CYP450 2C9 inhibitor Non-inhibitor 0.9144 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9039 CYP450 3A4 inhibitor Non-inhibitor 0.934 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7293 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.6495 Biodegradation Not ready biodegradable 0.9253 Rat acute toxicity 2.7846 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.536 hERG inhibition (predictor II) Inhibitor 0.6318
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Benzylethers / Trialkylamines / Dialkyl ethers / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Diphenylmethane / Benzylether / Tertiary aliphatic amine / Tertiary amine / Ether / Dialkyl ether / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amino compound, ether (CHEBI:4636) / a small molecule (CPD-10890)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Piao H, Nagai S, Tsurumaki T, Niki T, Higuchi H: Potentiation by neuropeptide Y of histamine H1 receptor-mediated contraction in rat blood vessels. Vascul Pharmacol. 2007 Apr;46(4):260-70. Epub 2006 Oct 27. [PubMed:17169617]
- Kesiova M, Alexandrova A, Yordanova N, Kirkova M, Todorov S: Effects of diphenhydramine and famotidine on lipid peroxidation and activities of antioxidant enzymes in different rat tissues. Pharmacol Rep. 2006 Mar-Apr;58(2):221-8. [PubMed:16702624]
- Hasala H, Moilanen E, Janka-Junttila M, Giembycz MA, Kankaanranta H: First-generation antihistamines diphenhydramine and chlorpheniramine reverse cytokine-afforded eosinophil survival by enhancing apoptosis. Allergy Asthma Proc. 2007 Jan-Feb;28(1):79-86. [PubMed:17390763]
- Wang Z, Woolverton WL: Self-administration of cocaine-antihistamine combinations: super-additive reinforcing effects. Eur J Pharmacol. 2007 Feb 28;557(2-3):159-60. Epub 2006 Dec 1. [PubMed:17196194]
- Ishikawa T, Takechi K, Rahman A, Ago J, Matsumoto N, Murakami A, Kamei C: Influences of histamine H1 receptor antagonists on maximal electroshock seizure in infant rats. Biol Pharm Bull. 2007 Mar;30(3):477-80. [PubMed:17329841]
- Havas TE, Cole P, Parker L, Oprysk D, Ayiomamitis A: The effects of combined H1 and H2 histamine antagonists on alterations in nasal airflow resistance induced by topical histamine provocation. J Allergy Clin Immunol. 1986 Nov;78(5 Pt 1):856-60. [PubMed:2878016]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Liu H, Zheng Q, Farley JM: Antimuscarinic actions of antihistamines on the heart. J Biomed Sci. 2006 May;13(3):395-401. [PubMed:16453179]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188]
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Connecticut's Official State Website: CYP Chart [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C18
- Uniprot ID
- P33260
- Uniprot Name
- Cytochrome P450 2C18
- Molecular Weight
- 55710.075 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873]
Drug created on June 13, 2005 07:24 / Updated on February 22, 2019 22:55